FURO[2,3-B]PYRIDINE-5-METHANOL → furo[2,3-b]pyridine-5-carbaldehyde

HRID 220268Notes

Reaction equation

HRID 220268 reaction equation
[O:1]1[C:5]2=[N:6][CH:7]=[C:8]([CH2:10][OH:11])[CH:9]=[C:4]2[CH:3]=[CH:2]1>C(Cl)Cl>[O:1]1[C:5]2=[N:6][CH:7]=[C:8]([CH:10]=[O:11])[CH:9]=[C:4]2[CH:3]=[CH:2]1

Participants

3

Reactant 1

HCID 10057661FURO[2,3-B]PYRIDINE-5-METHANOL

Product 1

HCID 10749327furo[2,3-b]pyridine-5-carbaldehydeYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.47 g of furo[2,3-b]pyridin-5-yl-methanol in 2 ml of DCM was added 10 ml of a Dess-Martins-Periodinane solution (15% in DCM). The reaction mixture was stirred overnight and then quenched with sat.-NaHCO3 and extracted with DCM. The organic phase was washed with brine, dried over MgSO4 and concentrated in vacuo. The resulting crude material was purified by CC using heptane/EtOAc 30/70 as eluant to yield 0.38 g of furo[2,3-b]pyridine-5-carbaldehyde as white solid.

Workup

  1. customquenched with sat.-NaHCO3
  2. extractionextracted with DCM
  3. washThe organic phase was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe resulting crude material was purified by CC

Sources & evidence

ORD record
ord-72e69c0e05bd49c99f6f65874f1003a6
Source dataset
uspto-grants-2012_06
Patent number
US08202885B2

Reaction notes

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